Proofpoint names Levey & Jaspal to leadership team. Tue, 8th Sep 2026 (Today) Proofpoint has appointed Brian Levey as Chief Legal Officer and Puja Jaspal as Chief People Officer, adding two executives to the cybersecurity company's leadership team. Levey will oversee the global legal organisation, including legal affairs, corporate governance, compliance, ethics and related strategic functions. Jaspal will lead the global people organisation, with responsibility for talent strategy, employee experience, organisational development and total rewards. The appointments come as Proofpoint expands its operations and adds senior leaders with experience at listed technology groups and large multinational companies. Both executives will work closely with the wider leadership team as the business develops internationally. Chief Executive Officer Sumit Dhawan said the hires reflect a broader period of change for the business. "Brian and Puja are exceptional leaders with deep experience helping global technology companies grow through periods of transformation," said Sumit Dhawan, Chief Executive Officer of Proofpoint. "Their leadership will help propel Proofpoint into its next era of growth-scaling our business, accelerating innovation, and setting the standard for how organizations protect people, data, and AI as the future of work is rewritten." Levey role Levey joins from Upwork, where he served as Chief Business Affairs & Chief Legal Officer. There, he oversaw legal, compliance, public policy and information security, and was involved in the company's initial public offering. Before Upwork, he spent more than 13 years at eBay, where he worked on strategic transactions including the acquisitions of PayPal, Skype, StubHub, Shopping.com and GSI Commerce. At Proofpoint, he will advise the executive leadership team and board while managing legal and governance matters across the business. His remit also includes risk management and trust-related issues involving customers, employees, partners and shareholders. Levey said the move continues a theme that has run through his in-house legal career. "Building trust online has been the through-line of my in-house career, and cybersecurity is where trust gets defended," said Brian Levey, Chief Legal Officer of Proofpoint. "Joining this leadership team at such a defining moment for the company is a real privilege, and I'm excited to help Proofpoint grow, innovate, and keep earning the confidence customers place in us every day." People brief Jaspal most recently served as Chief People Officer at Fastly, where she worked on business transformation and people strategy. Earlier in her career, she held senior leadership roles at Cisco, Visa and Google. At Proofpoint, she will oversee workforce strategy and organisational development as the company grows across multiple markets. The role also covers employee experience and compensation. The appointment puts an executive with experience across technology, financial technology and consumer products in charge of the group's people function. Jaspal has spent more than 25 years building organisations and leadership teams. Jaspal said the company's mission and culture shaped her decision to join. "Proofpoint's mission, culture, and commitment to innovation make this an incredibly meaningful and dynamic time to join the company," said Puja Jaspal, Chief People Officer of Proofpoint. "I'm looking forward to helping build an environment where exceptional talent can thrive, grow, and do their best work as we continue to scale and deliver for customers around the world." Growth context Proofpoint sells cybersecurity products focused on protecting communications, data and workplace tools used by employees and software agents. It says it works with more than 80 of the Fortune 100, more than 14,000 large enterprises and millions of smaller organisations. The hires reinforce core corporate functions alongside product and market expansion. They also reflect the operational demands facing technology businesses as they grow across jurisdictions, manage regulation and compete for skilled staff. Levey's background in board advisory work, compliance and major transactions brings experience often sought by private and public technology groups facing regulatory scrutiny and complex governance requirements. Jaspal's record at Fastly, Cisco, Visa and Google points to a focus on organisational design and workforce planning at scale. Both executives also bring academic credentials from major US institutions. Levey holds a J.D. from Stanford Law School and an A.B. in economics from Stanford University. Jaspal has a bachelor's degree in mechanical engineering from the University of Cincinnati and an MBA from Harvard Business School. Her remit includes helping create an environment where staff can grow as the company serves customers around the world.

Upwork cut a quarter of its staff while AI work on its platform grew 40%. Both numbers came from the same earnings cycle. If you freelance, one of them is about your market and the other is about your landlord, and confusing the two will cost you. Garvish Dua Founder, Kraftzen On 7 May 2026, Upwork cut about 24% of its workforce, roughly 145 to 150 people. CEO Hayden Brown wrote the memo herself. In the same earnings cycle, Upwork disclosed that AI-related work on its marketplace grew more than 40% year over year, with AI Integration and Automation up more than 50%, and AI gross services volume reaching $315 million. A company shrinking itself while the demand on its platform grows sounds like a contradiction. It is not. But if you freelance for a living, telling those two signals apart is the difference between a useful conclusion and a panic. What the memo actually said. Brown gave two reasons: speed and profitability. Not collapsing demand. Her framing of the AI part was direct: "Two pizza teams are dead." And: "AI means smaller, differently resourced teams in product and engineering can make a bigger impact than ever." She pointed to Upwork's 2024 layoff followed by strong 2025 execution as her evidence that smaller moves faster. The financial detail matters too. Upwork booked $16 million to $23 million in restructuring charges and issued softer revenue guidance for both Q2 and full-year 2026. That softer guidance is the honest bad news in this story, and it is a different thing from the demand figures. Read on. The two signals, separated. | Signal | Figure | What it is actually about | | Upwork headcount | -24%, about 145 to 150 roles | Upwork's own cost structure | | Restructuring charge | $16M to $23M | Upwork's balance sheet | | Revenue guidance | Softer for Q2 and FY2026 | Upwork's business, and a genuine warning | | AI work on the marketplace | +40% YoY | Your market | | AI Integration and Automation | +50% YoY | Your market, specifically | | AI gross services volume | $315M | Your market, in money | The rows are not measuring the same thing. Three describe a company. Three describe the demand flowing through it. "Upwork laid people off, therefore freelance AI work is drying up" is the wrong inference, and it is the one most coverage invites. The marketplace numbers say the opposite, and they come from the same disclosure. Upwork employing fewer people tells you about Upwork's cost structure. AI work growing 40% tells you about your pipeline. Only one of those is a fact about your market. Why both are true at once. A marketplace makes money by taking a cut of work that other people do. Its headcount and its volume are only loosely connected. Upwork can automate its own operations while its clients hire more freelancers. Support triage, matching, moderation, internal tooling: those are exactly the jobs AI is currently good at, and they are what a marketplace's staff largely do. Meanwhile the work clients are posting, integrating AI into a real business with real systems, is exactly the kind AI cannot yet do unsupervised. Brown was making a bet, and the bet is internally consistent even if you dislike it: AI removes the coordination overhead inside a company faster than it removes the specialist work outside one. The line that complicates her position. Separately, Brown has said that some companies are using AI as an excuse for layoffs to become more lean. She is not wrong, and she is also the CEO who cut 24% while citing AI-enabled smaller teams. Whether that is a contradiction or an unusually candid person describing a pattern she is part of, you can judge. It is worth reading her memo knowing she has said both things. For your purposes the useful part is the framing: "AI made this necessary" and "AI made this defensible" produce identical press releases. When you read any company's AI-driven restructuring, including this one, the number to look for is not the headcount. It is whether demand for the work moved. Here, it moved up. What this means if you freelance. The demand signal is good, and it is specific. AI Integration and Automation grew fastest, at over 50%. That is not prompt writing or content generation. It is connecting AI to systems a business already runs, which is skilled work with real deliverables. The platform risk signal is real, and it is separate. Softer guidance for Q2 and the full year is a statement about Upwork, and if Upwork is your only channel then Upwork's health is your risk. This is an argument for a second and third channel, not for panic. Do not price against the layoff news. Clients who read the headlines may arrive expecting AI to have made your work cheap. The same disclosure shows demand for that work rising 40%. Know the numbers before you discount. Kraftzen wrote a full post on pricing automation work, including why hourly billing pays you to be slow. Move up the stack. The categories growing fastest are integration and automation, which means owning an outcome inside a client's business rather than delivering a task. That is also the work least exposed to the next round of model improvements. Treat any platform as a lead source, not a business. Referrals, a site of your own and direct relationships are not exposed to one company's restructuring. Where to find work beyond one platform covers the alternatives. Common mistakes. Reading a marketplace's layoffs as a demand signal. Its headcount is about its cost structure. Its gross services volume is about your market, and those numbers moved in opposite directions here. Ignoring the guidance while celebrating the growth. Softer revenue guidance for Q2 and FY2026 is genuine bad news about Upwork specifically. Both halves deserve attention. Accepting lower rates because "AI made this easier". AI Integration and Automation demand grew over 50% year over year. Rising demand is not the setup for a discount. Depending on one platform. Upwork just demonstrated how quickly a platform's own priorities change. That is not a criticism of Upwork, it is an argument for channels it does not control. Competing on the tasks AI does well. The growth is in integration and automation, the parts that need judgement about somebody's actual business. Competing on the parts a model already handles is a race you are being asked to lose. Key takeaways. * On 7 May 2026 Upwork cut about 24% of staff, roughly 145 to 150 roles, with $16M to $23M in restructuring charges and softer guidance for Q2 and FY2026. * Hayden Brown cited speed and profitability, writing "Two pizza teams are dead" and arguing AI lets smaller teams do more. * In the same earnings cycle, AI-related marketplace work grew over 40% year over year, AI Integration and Automation grew over 50%, and AI gross services volume reached $315M. * Headcount describes Upwork's cost structure. Gross services volume describes your market. They are separate measurements and here they moved opposite ways. * Brown has separately said some companies use AI as an excuse for layoffs. "AI made this necessary" and "AI made this defensible" produce the same press release. * The fastest-growing category is integration and automation, which is skilled work connecting AI to systems a business already runs. * The real warning for freelancers is the softer guidance, not the layoffs. If one platform is your only channel, its business is your risk. Integration and automation work being the fastest-growing category matches what Kraftzen see from the other side of it, since connecting AI to systems a business already runs is most of what clients actually ask for. The demand is in the boring middle, not the demo. * careers * freelancing * upwork * ai